This invention provides methyl(methylthioethyl)-1,3-dioxolanes and oxathiolanes defined according to the generic structure: ##STR2## wherein X and Y represent sulphur or oxygen with the proviso that at least one of X and Y is oxygen; wherein m is 0 or 1; and wherein R.sub.1 and R.sub.2 are the same or different and each represent hydrogen or methyl and uses thereof in augmenting or enhancing the aroma or taste of foodstuffs.
Artificial flavoring agents for foodstuffs have received increasing attention in recent years. In many areas, such food flavoring agents are preferred over natural flavoring agents at least in part because of the uniform flavor that may be so obtained. For example, natural food flavoring agents and as extracts, essences, concentrates and the like are often subject to wide variation due to changes in the quality, type and treatment of the raw materials. Such variation can be reflected in the end product and results in unreliable flavor characteristics and uncertainty as to consumer acceptance and cost. Additionally, the presence of the natural product in the ultimate food may be undesirable because of increased tendency to spoil. This is particularly troublesome in convenience and snack food usage where such products as dips, soups, chips, prepared dinners, canned foods, sauces, gravies and the like are apt to be stored by the consumer for some time prior to use.
The fundamental problem in preparing artificial flavoring agents is that of achieving as nearly as possible to true flavor reproduction. This generally proves to be a difficult task since the mechanism for flavoring development in many foods is not understood. This is notable in products having beef broth-like, meat extract-like, hydrolyzed vegetable protein-like, roasted, pot roast, meaty, bloody, oniony, garlic, buttery and mushroom-like taste and aroma nuances.
Reproduction of beef broth-like, meat extract-like, hydrolyzed vegetable protein-like roasted, pot roast-like, meaty, bloody, oniony, garlic, buttery and mushroom aroma and taste nuances has been the subject of a long and continuous search by those engaged in the production of foodstuffs. The severe shortage of food, especially protein foods, in many parts of the world has given rise to the need for utilizing non-meat sources of proteins and making such proteins as palatable and as meat-like as possible. Hence, materials which will closely simulate or exactly reproduce the flavor and aroma of beef broth, hydrolyzed vegetable protein, yeast, meat, chicken soup, bread, garlic, onion and even pineapple and tomato are required. Furthermore, meat flavors and vegetable flavors have been enhanced previously by the use of such materials as monosodium glutamate. In many diets sodium is not desired. Furthermore, in many diets, the use of the glutamate ion or glutamic acid is not desired. Therefore a need has arisen for a monosodium glutamate replacer which does not have any glutamate ion present.
Moreover, there are a great many meat containing or meat based foods presently distributed in a preserved form. Examples of these are condensed soups, dry soup mixes, dry meat, freeze dried or lyophilized meats, packaged gravies and the like. While these products contain meat or meat extracts, the fragrance, taste and other organoleptic factors are often impaired by the processing operation and it is desirable to supplement or enhance the flavors of these preserved foods with versatile materials which have beef broth-like, meat extract-like, hydrolyzed vegetable protein-like, roasted, pot roast-like, meaty, bloody, onion, garlic and mushroom aroma and taste nuances.
Food flavors in the alkylthioalkanal area are known in the prior art. Thus, various 4-(methylthio)-butanal itself defined according to the structure: ##STR3## and the diethyl acetal thereof are known for augmenting or enhancing the aroma or taste of foodstuffs and other consumable materials as is taught in U.S. Letters Pat. No. 3,904,556 issued on Sept. 9, 1975 (the specification of which is incorporated by reference herein). Thus, the compound 4-(methylthio)-butanal diethyl acetal is taught in said U.S. Letters Pat. No. 3,904,556 to provide a mushroom, heated onion flavor with green sweet tomato, oniony and garlic nuances. The 4-(methylthio)-butanal itself is taught by said U.S. Letters Pat. No. 3,904,556 to provide a mushroom-like, tomato-like, vegetable-like, cheesey and fruity taste.
Alkanes having 3-methylthio moieties are known in the prior art, for example, that disclosed in Chem. Abstracts, Volume 96, No. 103327y having the structure: ##STR4## This abstract is of Tetrahedron Letters, Vol. 22, number 42, pages 4159-4162, 1981, (Title: "Thiosulfonium Ions. Methylthiolation of 3-methylthio-1-butene and cis- and trans-1-methylthio-2-butene": Kim and Caserio).
Chem. Abstracts, Vol. 96:20080m which is an abstract of Fischer, Liebigs Ann. Chem., 1981 (10), 1899-1902 discloses the compound having the structure: ##STR5## wherein n is 2, 3 or 4 but does not disclose its organoleptic utilities.
Chem. Abstracts, Vol. 84:164792v, (abstract of German Offenlegungsschrift No. 2,530,273) discloses the compound having the structure: ##STR6## but does not disclose its organoleptic utilities.
U.S. Letters Pat. No. 4,153,442 issued on May 8, 1979; U.S. Letters Pat. No. 4,224,051 issued on Sept. 23, 1980; and U.S. Letters Pat. No. 4,101,307 issued on June 18, 1978 each discloses plant growth regulating materials compounds defined according to the generic structure: ##STR7## in which X and Y which may be the same or different and represent oxygen, sulphur or a radical N-B where B is hydrogen, a lower alkyl radical containing 1 to 4 carbon atoms, an optionally substituted aryl radical or an optionally substituted acyl radical containing from 1 to 4 carbon atoms;
R and R' which may be the same or different and represent a lower alkyl radical containing from 1 to 4 carbon atoms or an acyl or amido radical containing from 1 to 4 carbon atoms; in addition they may form with ##STR8## a cycle corresponding to the formula ##STR9## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different and represent hydrogen, an alkyl radical containing from 1 to 4 carbon atoms and optionally substituted by a halogen, the radicals NO.sub.2, hydroxy or alkoxy containing from 1 to 4 carbon atoms;
A represents either a single bond or an alkylene chain containing from 1 to 4 carbon atoms optionally interrupted by an oxygen atom or a group N-B' where B' represents hydrogen, an optionally halogenated or hydroxylated alkyl group, an acyl group, the hydrocarbon portion of these radicals containing from 1 to 4 carbon atoms, or a cycle having in common with the preceding cycle 1 to 2 carbon atoms and containing from 3 to 6 carbon atoms, from 0 to 2 oxygen atoms and/or a group N-B, or a cycle corresponding to the formula ##STR10##
Included in this generic structure is the genus defined according to the structure: ##STR11## Specific compounds set forth in U.S. Letters Pat. No. 4,153,442, 4,224,051 and 4,101,307 are those having the structure: ##STR12## However, these patents do not specifically disclose the compound having the structure: ##STR13## These patents also do not set forth the criticality of these compounds insofar as their organoleptic utilities are concerned nor do they disclose any organoleptic utilities of such compounds.
Nagao, et al, Tetrahedron Letters No. 34, pages 3167-3168 (1979) discloses the genus of compounds defined according to the structure: ##STR14## in a synthetic route to yield certain ketones. In this genus R may be methyl, ethyl, propyl, butyl, tolyl, tolyl methoxy, allyl or phenyl. This genus is not part of the instant invention. Furthermore, the Nagao, et al paper does not disclose the organoleptic uses of such compounds.